Sodium Hydroxide → HCID 86615549, compound

HRID 605135Notes

Reaction equation

HRID 605135 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:24]=[CH:23][C:12]([C:13]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][CH:17]=3)=[O:14])=[CH:11][C:10]=2[NH:25][C:26]2[C:27]3[CH:35]=[CH:34][C:33]([CH:36]([CH3:38])[CH3:37])=[N:32][C:28]=3[N:29]=[CH:30][N:31]=2)=[CH:4][CH:3]=1.N([O-])=O.[Na+].[N-:43]=[N+:44]=[N-].[Na+].C([O-])(=O)C.[Na+].[OH-].[Na+]>Cl.O.C(OCC)(=O)C>[N:1]([C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:24]=[CH:23][C:12]([C:13]([NH:15][C:16]3[CH:17]=[CH:18][C:19]([Br:22])=[CH:20][CH:21]=3)=[O:14])=[CH:11][C:10]=2[NH:25][C:26]2[C:27]3[CH:35]=[CH:34][C:33]([CH:36]([CH3:38])[CH3:37])=[N:32][C:28]=3[N:29]=[CH:30][N:31]=2)=[CH:4][CH:3]=1)=[N+:43]=[N-:44]

Participants

9

Reactant 5

HCID 14798Sodium HydroxideHCID 33557Sodium AzideHCID 517045Sodium AcetateHCID 23668193Sodium NitriteHCID 67040834HCID 67040834, compound

Product 1

HCID 86615549HCID 86615549, compoundYield 32.2%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of the product of Example 13E (62.4 mg, 0.1066 mmol) in concentrated hydrochloric acid (2 mL) cooled to 0°-5° was treated dropwise with a solution of sodium nitrite (14.7 mg, 0.2131 mmol) in water (1 mL). After stirring at 0° for 1 hour, a solution of sodium azide (13.8 mg, 0.2131 mmol) and sodium acetate (72.6 mg, 0.885 mmol) in water (2 mL) was added dropwise at 0°, and the reaction stirred for 1 hour at 0°. The reaction was then diluted with water (25 mL) and ethyl acetate (50 mL), the aqueous pH was adjusted to 7-8 with 6N aqueous sodium hydroxide, the layers were separated, and the organic phase washed with brine (25 mL). The organic was dried over anhydrous sodium sulfate, filtered, and concentrated by rotary evaporation under vacuum. The resultant residue was purified by silica gel flash chromatography using 30% ethyl acetate/methylene chloride as eluent to afford the title compound as a yellow solid (21 mg, 32%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 1.34 (d, J=6.62 Hz, 6 H) 3.11-3.32 (m, 1 H) 7.10 (d, J=8.46 Hz, 2 H) 7.21 (d, J=8.46 Hz, 1 H) 7.41 (d, J=8.46 Hz, 2 H) 7.53 (d, J=8.82 Hz, 2 H) 7.63 (d, J=8.46 Hz, 1 H) 7.74 (d, J=9.19 Hz, 2 H) 7.81-7.91 (m, 1 H) 8.03 (d, J=1.10 Hz, 1 H) 8.58 (s, 1 H) 8.82 (d, J=8.46 Hz, 1 H) 10.23 (s, 1 H) 10.39 (s, 1 H); MS (ESI+) m/z 611/613 (M+H)+.

Workup

  1. stirringthe reaction stirred for 1 hour at 0°
  2. customthe layers were separated
  3. washthe organic phase washed with brine (25 mL)
  4. dry with materialThe organic was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated by rotary evaporation under vacuum
  7. customThe resultant residue was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-3bf66605946d4b91ab50cfb47f68ba3e
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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